EP2172118A2 - Compositions fluides contenant des polyphénols et leur procédé de préparation et d'emballage - Google Patents
Compositions fluides contenant des polyphénols et leur procédé de préparation et d'emballage Download PDFInfo
- Publication number
- EP2172118A2 EP2172118A2 EP09162642A EP09162642A EP2172118A2 EP 2172118 A2 EP2172118 A2 EP 2172118A2 EP 09162642 A EP09162642 A EP 09162642A EP 09162642 A EP09162642 A EP 09162642A EP 2172118 A2 EP2172118 A2 EP 2172118A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- resveratrol
- trans
- alcoholic
- retail
- beverage
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000008442 polyphenolic compounds Chemical class 0.000 title claims abstract description 24
- 235000013824 polyphenols Nutrition 0.000 title claims abstract description 24
- 239000000203 mixture Substances 0.000 title description 22
- 238000000034 method Methods 0.000 title description 15
- 238000004806 packaging method and process Methods 0.000 title description 15
- 239000012530 fluid Substances 0.000 title description 11
- 239000007864 aqueous solution Substances 0.000 claims abstract description 76
- 235000013361 beverage Nutrition 0.000 claims abstract description 69
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- LUKBXSAWLPMMSZ-OWOJBTEDSA-N Trans-resveratrol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(O)=CC(O)=C1 LUKBXSAWLPMMSZ-OWOJBTEDSA-N 0.000 claims description 196
- 235000018991 trans-resveratrol Nutrition 0.000 claims description 177
- 239000000843 powder Substances 0.000 claims description 7
- 230000005855 radiation Effects 0.000 claims description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 68
- 239000000243 solution Substances 0.000 description 61
- 230000001476 alcoholic effect Effects 0.000 description 50
- QNVSXXGDAPORNA-UHFFFAOYSA-N Resveratrol Natural products OC1=CC=CC(C=CC=2C=C(O)C(O)=CC=2)=C1 QNVSXXGDAPORNA-UHFFFAOYSA-N 0.000 description 29
- 229960005070 ascorbic acid Drugs 0.000 description 29
- 235000010323 ascorbic acid Nutrition 0.000 description 27
- 239000011668 ascorbic acid Substances 0.000 description 27
- 235000013334 alcoholic beverage Nutrition 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 235000021283 resveratrol Nutrition 0.000 description 19
- 229940016667 resveratrol Drugs 0.000 description 19
- 239000003381 stabilizer Substances 0.000 description 13
- -1 trans-resveratrol Chemical class 0.000 description 12
- XLAIWHIOIFKLEO-UHFFFAOYSA-N (E)-4-<2-(4-hydroxyphenyl)ethenyl>phenol Natural products C1=CC(O)=CC=C1C=CC1=CC=C(O)C=C1 XLAIWHIOIFKLEO-UHFFFAOYSA-N 0.000 description 10
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 10
- LUKBXSAWLPMMSZ-UPHRSURJSA-N Cis-resveratrol Chemical compound C1=CC(O)=CC=C1\C=C/C1=CC(O)=CC(O)=C1 LUKBXSAWLPMMSZ-UPHRSURJSA-N 0.000 description 10
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 239000000796 flavoring agent Substances 0.000 description 9
- 235000013355 food flavoring agent Nutrition 0.000 description 9
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 6
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- 239000000654 additive Substances 0.000 description 6
- XHEFDIBZLJXQHF-UHFFFAOYSA-N fisetin Chemical compound C=1C(O)=CC=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 XHEFDIBZLJXQHF-UHFFFAOYSA-N 0.000 description 6
- IYRMWMYZSQPJKC-UHFFFAOYSA-N kaempferol Chemical compound C1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 IYRMWMYZSQPJKC-UHFFFAOYSA-N 0.000 description 6
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- 239000011718 vitamin C Substances 0.000 description 6
- 239000011709 vitamin E Substances 0.000 description 6
- 235000019165 vitamin E Nutrition 0.000 description 6
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 5
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 5
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 5
- 229930003268 Vitamin C Natural products 0.000 description 5
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- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 5
- 238000006317 isomerization reaction Methods 0.000 description 5
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- 230000001681 protective effect Effects 0.000 description 5
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- HSTZMXCBWJGKHG-UHFFFAOYSA-N (E)-piceid Natural products OC1C(O)C(O)C(CO)OC1OC1=CC(O)=CC(C=CC=2C=CC(O)=CC=2)=C1 HSTZMXCBWJGKHG-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 description 4
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000013626 chemical specie Substances 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- TVQGDYNRXLTQAP-UHFFFAOYSA-N ethyl heptanoate Chemical compound CCCCCCC(=O)OCC TVQGDYNRXLTQAP-UHFFFAOYSA-N 0.000 description 4
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 235000005875 quercetin Nutrition 0.000 description 4
- 229960001285 quercetin Drugs 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- HSTZMXCBWJGKHG-CUYWLFDKSA-N trans-piceid Polymers O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(\C=C\C=2C=CC(O)=CC=2)=C1 HSTZMXCBWJGKHG-CUYWLFDKSA-N 0.000 description 4
- 229930013915 (+)-catechin Natural products 0.000 description 3
- 235000007219 (+)-catechin Nutrition 0.000 description 3
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 3
- PFTAWBLQPZVEMU-UKRRQHHQSA-N (-)-epicatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-UKRRQHHQSA-N 0.000 description 3
- 235000007355 (-)-epicatechin Nutrition 0.000 description 3
- 229930013783 (-)-epicatechin Natural products 0.000 description 3
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 3
- FTVWIRXFELQLPI-ZDUSSCGKSA-N (S)-naringenin Chemical compound C1=CC(O)=CC=C1[C@H]1OC2=CC(O)=CC(O)=C2C(=O)C1 FTVWIRXFELQLPI-ZDUSSCGKSA-N 0.000 description 3
- OALYTRUKMRCXNH-UHFFFAOYSA-N 5-pentyloxolan-2-one Chemical compound CCCCCC1CCC(=O)O1 OALYTRUKMRCXNH-UHFFFAOYSA-N 0.000 description 3
- UBSCDKPKWHYZNX-UHFFFAOYSA-N Demethoxycapillarisin Natural products C1=CC(O)=CC=C1OC1=CC(=O)C2=C(O)C=C(O)C=C2O1 UBSCDKPKWHYZNX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WEEGYLXZBRQIMU-UHFFFAOYSA-N Eucalyptol Chemical compound C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 3
- YXOLAZRVSSWPPT-UHFFFAOYSA-N Morin Chemical compound OC1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 YXOLAZRVSSWPPT-UHFFFAOYSA-N 0.000 description 3
- HSTZMXCBWJGKHG-CENDIDJXSA-N Piceid Natural products OC[C@@H]1O[C@@H](Oc2cc(O)cc(C=Cc3ccc(O)cc3)c2)[C@H](O)[C@H](O)[C@H]1O HSTZMXCBWJGKHG-CENDIDJXSA-N 0.000 description 3
- 102000000344 Sirtuin 1 Human genes 0.000 description 3
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- 240000006365 Vitis vinifera Species 0.000 description 3
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- KZNIFHPLKGYRTM-UHFFFAOYSA-N apigenin Chemical compound C1=CC(O)=CC=C1C1=CC(=O)C2=C(O)C=C(O)C=C2O1 KZNIFHPLKGYRTM-UHFFFAOYSA-N 0.000 description 3
- 235000008714 apigenin Nutrition 0.000 description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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Images
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D51/00—Closures not otherwise provided for
- B65D51/24—Closures not otherwise provided for combined or co-operating with auxiliary devices for non-closing purposes
- B65D51/28—Closures not otherwise provided for combined or co-operating with auxiliary devices for non-closing purposes with auxiliary containers for additional articles or materials
- B65D51/2807—Closures not otherwise provided for combined or co-operating with auxiliary devices for non-closing purposes with auxiliary containers for additional articles or materials the closure presenting means for placing the additional articles or materials in contact with the main contents by acting on a part of the closure without removing the closure, e.g. by pushing down, pulling up, rotating or turning a part of the closure, or upon initial opening of the container
- B65D51/2814—Closures not otherwise provided for combined or co-operating with auxiliary devices for non-closing purposes with auxiliary containers for additional articles or materials the closure presenting means for placing the additional articles or materials in contact with the main contents by acting on a part of the closure without removing the closure, e.g. by pushing down, pulling up, rotating or turning a part of the closure, or upon initial opening of the container the additional article or materials being released by piercing, cutting or tearing an element enclosing it
- B65D51/2828—Closures not otherwise provided for combined or co-operating with auxiliary devices for non-closing purposes with auxiliary containers for additional articles or materials the closure presenting means for placing the additional articles or materials in contact with the main contents by acting on a part of the closure without removing the closure, e.g. by pushing down, pulling up, rotating or turning a part of the closure, or upon initial opening of the container the additional article or materials being released by piercing, cutting or tearing an element enclosing it said element being a film or a foil
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Definitions
- the present invention relates to compositions comprising polyphenols and, in particular, to compositions comprising resveratrol.
- Trans-resveratrol and other naturally occurring polyphenols are believed to have a number of potential health benefits. Such benefits include protective effects against cardiovascular disease, neurodegeneration, and cancer. Trans-resveratrol and other plant phenols have also been shown to stimulate SIRT1, a sirtuin enzyme. It has been reported that increasing the activity level of SIRT1 increases life spans in a diversity of organisms.
- Trans-resveratrol is reported to occur in European red wines in amounts on the order of 0.5-5 mg/L. Additionally, pinot noir wines from the New York region are reported to contain up to 10 mg/L of trans-resveratrol. Moreover, trans-resveratrol quantities in non-alcoholic red wines are reported to be less than 4 mg/L.
- red wines include trans-piceattanol, fisetin, luteolin, kaempferol, quercetin, apigenin, naringenin, (+)-catechin, (-)-epicatechin, morin, and cis-resveratrol.
- red wines may be unattractive to some groups of individuals due to its alcohol content.
- groups of individuals can include people who are taking medications for which alcohol consumption is contraindicated, individuals that suffer from alcohol dependencies, people who suffer from depression, pregnant mothers, adolescents, and people that abstain from alcohol consumption as part of their preferred lifestyle.
- the polyphenol content of non-alcoholic beverages is significantly less than that of alcoholic beverages.
- the solubility and stability of polyphenols, specifically trans-resveratrol, in non-alcoholic, non-fermented aqueous solutions at concentrations comparable to quantities present in red wine have not been realized.
- the present invention provides a number of compositions, including non-alcoholic and non-fermented aqueous solutions comprising trans-resveratrol and/or other polyphenols.
- the present invention provides retail or commercially available beverages comprising trans-resveratrol and/or other polyphenols.
- the present invention additionally provides packaging operable to maintain the stability of trans-resveratrol in an alcohol-free, aqueous solution.
- the packaging may also be operable to maintain an acceptable level of trans-resveratrol stability between the time ofpackaging and the time of consumption or use of the trans-resveratrol solution.
- the present invention provides methods of producing aqueous solutions and/or retail beverages comprising trans-resveratrol as well as methods of increasing the solubility of trans-resveratrol in aqueous solution.
- the present invention provides a number of compositions, including non-alcoholic and/or non-fermented aqueous solutions comprising trans-resveratrol and/or other polyphenols.
- the present invention provides a fluid composition comprising an aqueous solution comprising trans-resveratrol in an amount greater than 30 mg/L.
- an aqueous solution comprises trans-resveratrol in an amount ranging from greater than 30 mg/L up to about 300 mg/L.
- an aqueous solution comprises trans-resveratrol in an amount ranging from about 50 mg/L to about 200 mg/L or from about 100 mg/L to about 150 mg/L.
- an aqueous solution comprises trans-resveratrol in an amount greater than about 300 mg/L.
- a fluid composition comprises an aqueous solution comprising trans-resveratrol in an amount greater than 5 mg/L to about 30 mg/L.
- an aqueous solution comprising trans-resveratrol in any of the amounts provided herein comprises ethanol in an amount less than about 5 percent by volume. In other embodiments, an aqueous solution comprises ethanol in an amount less than about 2 percent by volume. In another embodiment, an aqueous solution comprising trans-resveratrol in any of the amounts recited herein comprises ethanol in an amount less than about 1 percent by volume. In a further embodiment, an aqueous solution comprises ethanol in an amount less than about 0.5 percent by volume. In one embodiment, an aqueous solution comprising trans-resveratrol in any of the amounts provided herein does not comprise ethanol and/or other alcohol(s).
- an aqueous solution comprising trans-resveratrol in any of the amounts provided herein further comprises at least one stabilizing agent.
- an aqueous solution comprises a plurality of stabilizing agents.
- Stabilizing agents comprise chemical species operable to enhance the stability of trans-resveratrol in aqueous solution by inhibiting or preventing the geometric isomerization of trans-resveratrol to the cis-isomer.
- stabilizing agents minimize and/or eliminate elements or species that facilitate the conversion of trans-resveratrol to cis-resveratrol.
- stabilizing agents comprise nitrogen, carbon dioxide, or mixtures thereof. In other embodiments, stabilizing agents comprise vitamin A, vitamin C, vitamin E, or mixtures thereof. In some embodiments, an aqueous solution comprising trans-resveratrol comprises vitamin C in an amount of up to about 1000 mg/L. In another embodiment, an aqueous solution comprising trans-resveratrol comprises vitamin A in an amount ranging from about 1 to about 6,250 International Units (IU's) or from about 2,100 IU's to about 4,200 IU's. In a further embodiment, an aqueous solution comprising trans-resveratrol comprises vitamin E in an amount ranging from about 1 to about 125 IU's or from about 12.5 to about 125 IU's.
- IU's International Units
- an aqueous solution comprising trans-resveratrol comprises vitamin E in an amount ranging from about 1 to about 125 IU's or from about 12.5 to about 125 IU's.
- an aqueous solution in some embodiments of the present invention, can comprise trans-resveratrol in any amount recited herein for a time period of at least six months from the preparation of the aqueous solution.
- an aqueous solution comprises greater than 30 mg/L up to about 300 mg/L of trans-resveratrol at least six months after preparation of the aqueous solution.
- an aqueous solution comprises trans-resveratrol in an amount greater than 5 mg/L to about 30 mg/L at least six months after preparation of the solution. In another embodiment, an aqueous solution comprises trans-resveratrol in any amount provided herein for a time period of at least 9 months after preparation of the solution.
- an aqueous solution comprising trans-resveratrol in any of the amounts recited herein further comprises other polyphenols including, but not limited to, trans-piceattanol, fisetin, luteolin, kaempferol, quercetin, apigenin, naringenin, (+)-catechin, (-)-epicatechin, morin, and cis-resveratrol.
- aqueous solutions comprising trans-resveratrol do not comprise cis-resveratrol.
- emulsifying agents are employed to further enhance the dispersion of trans-resveratrol in aqueous solution.
- Suitable emulsifying agents comprise calcium carbonate, lecithin, methylcellulose, mono- and diglycerides, pectin and phosphoric acid.
- Aqueous solutions comprising trans-resveratrol in some embodiments, have a pH ranging from about 2.5 to about 7. In other embodiments, aqueous solutions comprising trans-resveratrol have a pH ranging from about 2.5 to about 4.5. In a further embodiment, aqueous solutions comprising trans-resveratrol have a pH ranging from about 3 to about 4.
- the present invention provides retail beverages comprising trans-resveratrol.
- the present invention provides a retail beverage comprising trans-resveratrol in an amount ranging from about 5 mg/L to about 300 mg/L, wherein the retail beverage is non-alcoholic.
- non-alcoholic refers to an alcohol (ethanol) content of the beverage less than about 0.5% by volume.
- a non-alcoholic retail beverage comprises trans-resveratrol in an amount ranging from about 10 mg/L to about 300 mg/L or from about 30 mg/L to about 250 mg/L.
- a non-alcoholic retail beverage comprising trans-resveratrol in any of the amounts provided herein further comprises at least one stabilizing agent.
- a non-alcoholic retail beverage comprises a plurality of stabilizing agents.
- stabilizing agents for use in retail beverages comprising trans-resveratrol comprise vitamin A, vitamin C, vitamin E, or combinations thereof.
- a non-alcoholic retail beverage comprising trans-resveratrol further comprises vitamin C in an amount of up to about 1000 mg/L.
- a non-alcoholic retail beverage comprising trans-resveratrol further comprises vitamin A in an amount ranging from about 1 to about 6,250 IU's or from about 2,100 to about 4,200 IU's.
- a non-alcoholic retail beverage comprising trans-resveratrol further comprises vitamin E in an amount ranging from about 1 to about 125 IU's or from about 12.5 to about 125 IU's.
- stabilizing agents suitable for use in non-alcoholic retail beverages comprising trans-resveratrol comprise chemical species operable to absorb ultra-violet radiation.
- a non-alcoholic retail beverage in some embodiments of the present invention, can comprise trans-resveratrol in any amount recited herein for a time period of at least six months from the preparation of the non-alcoholic retail beverage.
- an aqueous solution comprises from about 5 mg/L up to about 300 mg/L of trans-resveratrol at least six months after the aqueous solution is prepared.
- a non-alcoholic retail beverage comprises trans-resveratrol in an amount greater than 5 mg/L to about 30 mg/L at least six months after preparation of the non-alcoholic retail beverage. In another embodiment, a non-alcoholic retail beverage comprises trans-resveratrol in any amount provided herein for a time period of at least 9 months after preparation of the solution.
- flavoring agents comprise methyl salicylate, allyl cyclohexylpropionate, citral, citronellal, citronellol, 1,8-cineole (eucalyptol), cinnamyl alcohol (cinnamic alcohol), cinnamaldehyde (cinnamic aldehyde), decanal (decyl aldehyde), decanol (decyl alcohol), ethyl dicanoate (ethyl caprate), terpineol, ⁇ -nonalactone (nonalactone), vanillin, p-methylacetophenone, hydroxycitonellal, hydroxycitronellal dimethylacetate, piperonal (heliotropine), isoamyl phenlacetate, isobutyl phenylacetate, ethyl penylacetate, propionic acid, isoamyl propionate, ethyl propionate, benz
- flavoring agents comprise benzyl alcohol, benzaldehyde, d-bomeol, maltol, methyl N-methylanthranilate, methyl b-naphthyl ketone, dl- menthol (dl-peppermint camphor), l -menthol (peppermint camphor), butyric acid, isoamyl butylate, ethyl butyrate, cyclohexyl butyrate, butylrate, or linalool (linalol) or combinations thereof.
- Non-alcoholic retail beverages comprising trans-resveratrol in some embodiments, have a pH ranging from about 3 to about 7. In other embodiments, non-alcoholic retail beverages comprising trans-resveratrol have a pH ranging from about 3.5 to 4.5.
- a non-alcoholic retail beverage comprising trans-resveratrol has no calories.
- a non-alcoholic retail beverage comprising trans-resveratrol has from about 1 to about 200 calories per serving.
- a non-alcoholic retail beverage comprising trans-resveratrol has from about 10 to about 150 or from about 25 to about 100 calories per serving.
- a non-alcoholic retail beverage comprising trans-resveratrol has from about 50 calories to about 75 calories per serving.
- Non-alcoholic retail beverages comprising trans-resveratrol in any of the amounts recited herein, in some embodiments, are teas.
- a non-alcoholic retail beverage comprising trans-resveratrol is an energy or sports drink operable to replenish electrolytes and/or carbohydrates.
- a non-alcoholic retail beverage comprising trans-resveratrol is yogurt or a "smoothie" type fluid composition.
- a non-alcoholic retail beverage comprising trans-resveratrol is a cola or other acidic carbonated soft drink.
- Yet another embodiment of a non-alcoholic beverage comprising trans-resveratrol is coffee.
- a retail alcoholic beverage comprises trans-resveratrol in an amount greater than 15 mg/L. In another embodiment, a retail alcoholic beverage comprises trans-resveratrol in an amount ranging from greater than about 15 mg/L to about 2.5 g/L. In some embodiments, a retail alcoholic beverage comprises trans-resveratrol in an amount ranging from about 20 mg/L to about 1 g/L or from about 50 mg/L to about 750 mg/L.
- a retail alcoholic beverage comprising trans-resveratrol in any of the amounts recited herein is a beer or malt beverage.
- a retail alcoholic beverage comprising trans-resveratrol in any of the amounts provided herein is a wine, wherein a wine comprises a white wine, a red wine, or a mixture thereof.
- a retail alcoholic beverage comprising trans-resveratrol in any of the amounts provided herein is a liquor.
- Retail alcoholic beverages comprising trans-resveratrol can further comprise any of the additional components provided herein for non-alcoholic retail beverages including, but not limited to, stabilizing agents, additional polyphenols, flavoring agents, and/or emulsifying agents.
- retail alcoholic beverages comprising trans-resveratrol can have caloric contents consistent with those recited herein for non-alcoholic retail beverages.
- an alcoholic retail beverage in some embodiments of the present invention, can comprise trans-resveratrol in any amount recited herein for a time period of at least six months from the preparation of the alcoholic retail beverage.
- a retail alcoholic beverage comprises greater than 15 mg/L up to about 2.5 g/L of trans-resveratrol at least six months after the retail alcoholic beverage is prepared.
- a retail alcoholic beverage comprises trans-resveratrol in an amount ranging from about 20 mg/L to about 750 mg/L at least six months after preparation of the retail alcoholic beverage.
- a retail alcoholic beverage comprises trans-resveratrol in any amount provided herein for a time period of at least 9 months after preparation of the solution.
- Retail alcoholic beverages are available for purchase at commercial outlets including, but not limited to, grocery stores, drug stores, convenience stores, health specialty stores, and/or alcohol beverage control establishments.
- Trans-resveratrol for use in aqueous solutions, non-alcoholic retail beverages, and retail alcoholic beverages can be obtained from a synthesized source or, alternatively, as plant or natural food extract. Methods of trans-resveratrol synthesis and extraction are well known to those in the art. Extraction of trans-resveratrol, for example, can be obtained from grape seeds, grape skin, grape pumace, and Japanese Knotweed ( Polygonum cuspidatum ).
- trans-resveratrol for use in aqueous solutions, non-alcoholic retail beverages, and retail alcoholic beverages of the present invention is in the 3- ⁇ -glucoside form of trans-resveratrol.
- This form of trans-resveratrol is 2-[3-hydroxy-5-[( E )-2-(4-hydroxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol, otherwise known as polydatin or piceid.
- the bioavailability of the trans-resveratrol derived from the ⁇ -glucosidic form is equivalent to the free form of trans-resveratrol in solution.
- Concentrations of piceid in aqueous solutions, retail non-alcoholic, and retail alcoholic beverages of the present invention are determined such that the quantity of free trans-resveratrol released upon hydrolysis remains within the trans-resveratrol ranges set forth herein.
- the present invention provides packaging for aqueous solutions, non-alcoholic retail beverages, and retail alcoholic beverages comprising trans-resveratrol operable to enhance the stability of trans-resveratrol in solution by inhibiting geometric isomerization to cis-resveratrol.
- Aqueous solutions and retail beverages disclosed herein comprising trans-resveratrol can be contained within and protected from exposure to UV radiation by a plastic bottle material, e.g., specific grades of polyethylene terephthalate (PET) well known to those in the art, which have specialized additives for blocking a specific range ofUV wavelengths while maintaining a "clear" bottle appearance.
- a plastic bottle material e.g., specific grades of polyethylene terephthalate (PET) well known to those in the art, which have specialized additives for blocking a specific range ofUV wavelengths while maintaining a "clear" bottle appearance.
- colorants can also be added to the plastic or glass bottling material to provide further protection of the contents against UV-degradation. These additives may block or absorb UV light in certain wavelengths.
- aqueous solutions and/or retail beverages of the present invention are packaged in cans including, but not limited to, aluminum cans, steel cans with a polymeric film liner, or multi-layer aseptic paper/plastic packaging such as packaging commercially available from Tetra Pak of Switzerland.
- Trans-resveratrol + ascorbic acid 100 ml of water was heated to about 90°C in a glass beaker. 6 mg of trans-resveratrol extract (99%, Abatra Lot #0606231) was added to the heated water with a hand blender to produce a solution having a trans-resveratrol concentration of 60 mg/L. 600 mg of ascorbic acid (powder) L-ascorbic acid (powder) from BDH, distributed exclusively for VWR, 99.7% pure, lot #45335635, was added to the trans-resveratrol solution with mild stirring to produce an ascorbic acid concentration of 6 g/L.
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Mechanical Engineering (AREA)
- Botany (AREA)
- Mycology (AREA)
- Non-Alcoholic Beverages (AREA)
- Packging For Living Organisms, Food Or Medicinal Products That Are Sensitive To Environmental Conditiond (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Wrappers (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US81314706P | 2006-06-13 | 2006-06-13 | |
EP07796042A EP2035538A2 (fr) | 2006-06-13 | 2007-06-13 | Formules de fluides comprenant des polyphénols et méthodes de fabrication et d'emballage desdites formules |
Related Parent Applications (2)
Application Number | Title | Priority Date | Filing Date |
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WOPCT/US2007/013842 Previously-Filed-Application | 2007-06-13 | ||
EP07796042.5 Division | 2007-06-13 |
Publications (2)
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EP2172118A2 true EP2172118A2 (fr) | 2010-04-07 |
EP2172118A3 EP2172118A3 (fr) | 2011-09-07 |
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ID=38736081
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
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EP09162642A Withdrawn EP2172118A3 (fr) | 2006-06-13 | 2007-06-13 | Compositions fluides contenant des polyphénols et leur procédé de préparation et d'emballage |
EP07796042A Withdrawn EP2035538A2 (fr) | 2006-06-13 | 2007-06-13 | Formules de fluides comprenant des polyphénols et méthodes de fabrication et d'emballage desdites formules |
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Application Number | Title | Priority Date | Filing Date |
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EP07796042A Withdrawn EP2035538A2 (fr) | 2006-06-13 | 2007-06-13 | Formules de fluides comprenant des polyphénols et méthodes de fabrication et d'emballage desdites formules |
Country Status (3)
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US (1) | US20080213433A1 (fr) |
EP (2) | EP2172118A3 (fr) |
WO (1) | WO2007146318A2 (fr) |
Cited By (1)
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ITPI20110063A1 (it) * | 2011-06-08 | 2012-12-09 | Funcional Food Res S R L | Bevanda alcolica ad elevato contenuto di resveratrolo e metodo di produzione relativo. |
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MX343357B (es) * | 2007-09-07 | 2016-11-03 | Invinity Llc | Bebida a base de vino no alcoholica. |
WO2009056212A1 (fr) * | 2007-10-29 | 2009-05-07 | Dsm Ip Assets B.V. | Compositions contenant du resvératrol et de la pectine |
US20130243928A1 (en) * | 2007-10-31 | 2013-09-19 | Philip Anthony Norrie | Resveratrol Enhanced Wine |
CA2711734A1 (fr) | 2008-01-08 | 2009-07-16 | David Rubin | Compositions et procede d'administration de resveratrol et de pterostilbene |
CA2732795C (fr) * | 2008-06-11 | 2016-08-09 | Susanne Gardner | Boissons composees de composants a base de vin |
KR101657326B1 (ko) | 2009-02-04 | 2016-09-19 | 디에스엠 아이피 어셋츠 비.브이. | 레스베라트롤 조성물 |
US20090196951A1 (en) * | 2009-03-16 | 2009-08-06 | Ross Brandborg | Product and Method for Alcoholic Beverage Infused with Resveratrol |
WO2010135589A2 (fr) * | 2009-05-20 | 2010-11-25 | Sakura Properties, Llc | Boisson constituant un complément alimentaire et servant à l'administration de resvératrol et d'autres polyphénols |
WO2010138584A1 (fr) * | 2009-05-27 | 2010-12-02 | Cliff Oster | Produit de type boisson contenant du resvératrol |
CA2769278A1 (fr) * | 2009-08-10 | 2011-02-17 | Stokely-Van Camp, Inc. | Procede pour mettre un flavonoide en suspension dans une boisson |
ITMI20091940A1 (it) | 2009-11-05 | 2011-05-06 | Functional Point S R L | Composizione comprendente resveratrolo e almeno un polifenolo del vino rosso e suoi usi. |
EP2776549B1 (fr) * | 2011-11-11 | 2018-01-10 | Red Dawn Ip Holdings (Pty) Ltd. | Procédé amélioré pour la fabrication de boissons alcooliques |
WO2013183177A1 (fr) * | 2012-06-07 | 2013-12-12 | 株式会社燦樹 | Composition de jaune d'œuf à l'ail et son procédé de production |
US9358216B2 (en) | 2014-08-02 | 2016-06-07 | Heart Healthy Spirits, LLC | Tincture for infusing resveratrol and methods of use |
US9763895B2 (en) | 2014-08-02 | 2017-09-19 | Heart Healthy Spirits, LLC | Tincture for infusing flavonoids and methods of use |
IT201700096298A1 (it) | 2017-08-25 | 2019-02-25 | Penta Holding | Metodo per la produzione di una composizione polifenolica a partire da malto d’orzo |
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- 2007-06-13 WO PCT/US2007/013842 patent/WO2007146318A2/fr active Application Filing
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Also Published As
Publication number | Publication date |
---|---|
EP2035538A2 (fr) | 2009-03-18 |
WO2007146318A2 (fr) | 2007-12-21 |
EP2172118A3 (fr) | 2011-09-07 |
WO2007146318A9 (fr) | 2008-03-13 |
WO2007146318A3 (fr) | 2009-04-09 |
US20080213433A1 (en) | 2008-09-04 |
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